15 Worst Contracts in American Sports History

Isiah Thomas, New York Knicks

Contract: Four years, $24 million

The worst-ever front office contract. After signing malcontents and overrated players such as Jerome James and Stephon Marbury to outlandish contracts, hemorrhaging money, paying Larry Brown over $28 million to lead the Knicks to a 23-59 record, failing miserably as a coach as well as team president, and dragging the Knicks through a humiliating sexual harassment trial, the Knicks awarded Thomas with a four-year, $24 million deal. —Johnny Goodtimes (AP Photo/Ed Betz)

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More from this Slideshow

15 Worst Contrac...Last week, the Eagles signed Michael Vick to a six-year, $100 million contract. That's a ton of cash to pay to a QB who has a grand total of two playoff wins and whose running skills should be eroded six years from now. Furthermore, as we shall learn in this slideshow, six-year contracts don't tend to work out too well. But Vick would have to play pretty poorly to land on this list... sort of like he played after he signed his last $100 million contract.—Johnny Goodtimes (AP Photo/Alex Brandon)

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The last time a team signed Vick to an outrageous contract, it didn’t turn out so well. The Falcons signed Vick to a 10-year, $130 million deal in 2005, with $37 million guaranteed. For their money, they got a 15-15 record, a guy who completed 54 percent of his passes, and ultimately a felon.—Johnny Goodtimes (AP Photo/Nick Wass)

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After a brief burst in the playoffs, James was signed to an outlandish contract with the Knicks. It was lambasted the day it was made, and the critics were more than vindicated. James was thrilled with the big money, so much so that he decided to quick working out, and he reported to camp overweight and indifferent. The highlight of his Knicks career came in 2005-2006, when he averaged 3 PPG. In his final two years on the Knicks he scored a grand total of 10 points.—Johnny Goodtimes (AP Photo/Tom Strickland)

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The six-year deal almost never fails to fail spectacularly. And when it comes to laugh-out-loud stupid contracts, the Knicks never fail to deliver belly laughs. Houston played fairly well for the first two years of the contract, but knee problems quickly derailed his career. In the final two years of the deal, Houston did not play a single game. But since the contract was guaranteed, he was still the second-highest paid player in the league, despite scoring as many points as I did. —Johnny Goodtimes (AP Photo/Mike Groll)

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This one is just mind-blowing. The highest paid safety in NFL history when he signed the contract, Archuleta ended up starting seven games before being relegated to special teams duty. He was traded to the Bears for a sixth round pick after one season. —Johnny Goodtimes (AP Photo/Gerald Herbert)

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Redden’s numbers were already in a steep decline when he became a free agent in 2008. That’s why the Rangers’ offer of six years and $39 million had many New Yorkers wondering if Isaiah Thomas had been somehow involved. By 2010, Redden was playing in the American Hockey League, by far the highest paid player in that league’s history. —Johnny Goodtimes (AP Photo/Frank Franklin II)

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It didn’t take long for the Raiders to realize what a huge mistake they had made when they signed the Falcons star in 2008. He lasted all of eight games and made $8 million for his eight weeks of service before being released by the Raiders. —Johnny Goodtimes (AP Photo/Eric Risberg, File)

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The Suns realized soon after signing Marbury that if they freed up cap space they could get their hands on Steve Nash, a far better point guard. But who would take a whiner, malcontent and awful teammate off their hands for that much money? Enter Isaiah Thomas. Two weeks after becoming President of the Knicks, Thomas started his astounding streak of signing every overrated, overpaid player he could get his hands on. The Suns got Nash and became a perennial contender. The Knicks got Marbury, who whined and behaved like a petulant child for most of his time in New York, threatened coaches when they wouldn’t start him, and never led the team to a playoff win. —Johnny Goodtimes (AP Photo/Stephen J. Boitano)

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In the Summer of 2010, Dwyane Wade, LeBron James and Amar’e Stoudemire were all free agents. None of them signed for as much money as Joe Johnson. But it all paid off in the 2010-2011 season, when Johnson established himself as the best player in the NBA. Hahaha! I’m kidding. Johnson is a serviceable scorer on a slightly above average team. Apparently that’s worth around $20 million a year. —Johnny Goodtimes (AP Photo/John Bazemore)

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When the Mets signed Bonilla to a five-year, $29 million deal in 1991, they made him the richest player in baseball. His time with the Mets would be tumultuous, but fairly productive. It was when he came back to the Mets in 1999 that things went straight downhill. He spent most of the season arguing with manager Bobby Valentine, and at the end of the year the Mets decided to buy out his contract. However, instead of paying him a lump sum of the $5.9 million they owed him, they decided to defer payment on the contract until 2011, and then pay him over a million a year for 25 years, assuming an interest rate of 8 percent. Therefore, the 47-year-old Bonilla is making almost three times as much money this year as starting Mets catcher Josh Thole. —Johnny Goodtimes (AP Photo)

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The Yanks have won a lot of titles, but they’ve paid more money to bums than any team in sports history. They grossly overpaid for Danny Tartabull, Hideki Irabu, Carl Pavano and Jason Giambi. But the worst contract they’ve doled out went to Burnett. The one-time Marlin and Blue Jay star has been a total dud in New York, where he’s gone 32-35 with a 4.81 ERA. And there are still two years left on his enormous contract. Good thing money grows on trees in the Bronx. —Johnny Goodtimes (AP Photo/Nam Y. Huh)

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A Cy Young Award winner and three-time All-Star with the Oakland A’s, Zito went across the Bay to San Francisco in 2007, signing an astronomical seven-year deal. He has been a complete dud in San Fran. In Oakland, he went 102-63 with a 3.55 ERA. In San Fran, he’s 41-63 with a 4.52 ERA. His strikeouts have dropped dramatically, as has the velocity on his fastball. He was so bad in 2010 that the Giants left him off their playoff roster. He was even worse in 2011 before having his season cut short by a foot injury. And there are still two years left on his contract. —Johnny Goodtimes (AP Photo/Gus Ruelas)

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Four years after going 20-5 with a 2.97 ERA with the Braves, Neagle’s ship came in. He signed a lucrative deal with the Rockies, and he and Mike Hampton were expected to lead the team to the promised land. His time with the Rockies was, like Hampton’s, a disaster. He went 19-23 with a 5.57 ERA in three seasons. There was some good news for the Rockies, however. After three disastrous seasons, they were able to void the contract. They had thought to include a morals clause, and getting caught in a compromising position with a hooker in 2004 violated the contract. He never pitched again in the Major Leagues. —Johnny Goodtimes (AP Photo/Ed Andrieski)

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An atrocious contract, it crippled the Islanders’ front office and made Yashin untradeable. He was so awful by 2007 that the Islanders bought out his contract for over $17 million. He has played the last several years in Russia, but there have been talks of him rejoining the Islanders in 2011. I’m serious. —Johnny Goodtimes (AP Photo/Kevork Djansezian)

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The Rockies, coming off an 82-80 season in 2000, thought that if they signed a couple of big name free agent pitchers, they would be World Series champions. And so they made it rain on Mike Hampton. Bad move. Hampton was awful for the Rockies. The first year of his contract, he had an ERA over 5. The second year, he went 7-15 with a 6.15 ERA. The Rockies agreed to eat part of his salary to send him out of town to the Braves, who hoped that he would return to the form he had shown with the Astros in the late 1990s. After a promising start to 2003, injuries ruined the rest of his career, and he missed two full seasons after back-to-back Tommy John surgeries. Much of his salary ended up being covered by insurance policies. —Johnny Goodtimes (AP Photo/David Zalubowski)

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No matter how mediocre Joe Johnson is, his six-year deal will almost certainly be better than the one Gilbert Arenas signed with the Washington Wizards in 2008. Since signing the contract, Arenas has struggled with knee problems, set a franchise record for most turnovers in a game (12), brought guns to the locker room, was suspended by the NBA for 50 games, faked injury in a preseason game and was traded to Orlando, where he averaged a mere 8 PPG. It has been a spectacular fall from grace. —Johnny Goodtimes (AP Photo/Alan Diaz)

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Sort of. One of the most confusing contracts in the history of sports, Young signed a deal with the L.A. Express that paid him $40 million over 43 years. The way the Express did that was to set up his 10-year, $40 million deal as an annuity that would stretch out over 43 years, starting at $200,000 in 1990 and going up to over $3 million by 2027. Therefore, the bad contract wasn’t inked by the Express, who would no longer exist a mere two years after the contract was signed. The loser in this deal was whatever investment organization agreed to take on the annuity (they will supposedly continue paying Young over $1 million a year until 2027). Or will they? An L.A. Times article from 1985 says that Young bought out the annuity for $1.4 million, but a 2006 ESPN article says that he’s still being paid. So what’s the truth? Only Steve Young and his accountant are aware of that. —Johnny Goodtimes (AP Photo/Paul Sakuma)

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The worst-ever front office contract. After signing malcontents and overrated players such as Jerome James and Stephon Marbury to outlandish contracts, hemorrhaging money, paying Larry Brown over $28 million to lead the Knicks to a 23-59 record, failing miserably as a coach as well as team president, and dragging the Knicks through a humiliating sexual harassment trial, the Knicks awarded Thomas with a four-year, $24 million deal. —Johnny Goodtimes (AP Photo/Ed Betz)

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The worst-ever coaching contract. Since Dan Snyder took over, the Redskins have rewritten the book on how to do everything wrong (see our "Worst Franchises" slideshow). One of their most dubious mistakes was letting Marty Schottenheimer go after the ‘Skins won 8 of their final 11 games of the 2001 season. They had to pay Schottenheimer $5 million of his contract when they fired him so that they could bring in Steve Spurrier for $5 million a year. Spurrier led the Redskins to a 12-20 record over two seasons, then quit. The Redskins currently have the second-highest paid coach in football (Mike Shanahan) who makes $7 million a year and led the team to a 6-10 record last season. —Johnny Goodtimes (AP Photo/Koji Sasahara)

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The Silna Brothers owned the Spirits of St. Louis in the ABA, and when the ABA merged with the NBA, the duo hoped that the Spirits would join the league. They weren’t invited to be one of the four teams, however. They agreed to fold the Spirits if they were paid $2.2 million… and a 1/7th share of television revenues for the four teams entering the NBA from the ABA (The Nets, Nuggets, Pacers and Spurs). At the time, the NBA was rarely on TV, and little was thought of that addendum. But the NBA exploded nationally in the 80s and 90s, and the Silna Brothers have made over $200 million from the NBA over the past 35 years for doing absolutely nothing. (Pictured: Ozzie Silna) —Johnny Goodtimes (AP Photo/Damian Dovarganes)

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